Shelter Island Holidays from £1,116

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Your Shelter Island Holiday

Lock in a Shelter Island holiday package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighbourhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organising a tailored Shelter Island holiday is a cinch with Expedia.

Top Shelter Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Ridge Hotel

The Ridge Hotel

3 out of 5
Manhattan
Price was £2,176, price is now £1,116 per person
£1,116
per person
15 Jun - 18 Jun
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.2/10 Very Good! (1,117 reviews)
The staff Wilma was exceptional very helpful with directions transportation and restaurant referrals. Bed was too firm and uncomfortable

Reviewed on 14 May 2026

YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Manhattan
Price was £2,010, price is now £1,136 per person
£1,136
per person
15 Jun - 18 Jun
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
7.8/10 Good! (2,781 reviews)
The location of the hotel was excellent.

Reviewed on 14 May 2026

Hilton New York Times Square

Hilton New York Times Square

4 out of 5
Manhattan
Price was £2,374, price is now £1,423 per person
£1,423
per person
14 Jun - 17 Jun
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.6/10 Excellent! (1,902 reviews)
We enjoyed our stay at this Hilton location. The room was very spacious compared to other manhattan hotels. The property is I a great location, close to many attractions and food options. No excessive noise despite being in the heart of the city. The staff was great but especially the first level bag/concierge gentlemen. They were especially friendly and handled our items with care. We were also running late to our train but thanks to one gentleman’s quick service we were able to make it on time.

Reviewed on 13 May 2026

The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Price was £3,080, price is now £1,924 per person
£1,924
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
great time thank you

Reviewed on 12 May 2026

Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was £4,352, price is now £2,739 per person
£2,739
per person
25 Jul - 1 Aug
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (7 reviews)
Courteous and friendly staff

Reviewed on 4 Nov 2025

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Mashomack Preserve.

Find hotels in Menantic Creek

Shelter Island Beach Holiday

There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
East Hampton Main Beach, Wolffer Estates Vineyard and 67 Steps Beach

Top hotels in Shelter Island

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is £499 per night from 17 May to 18 May
£499
17 May - 18 May
includes taxes & fees
8.4/10 Very Good! (779 reviews)
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!

Reviewed on 11 May 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is £153 per night from 18 May to 19 May
£153
18 May - 19 May
includes taxes & fees
9.2/10 Wonderful! (1,343 reviews)
Cute place great views would go back in the summer

Reviewed on 11 May 2026

Montauk Manor
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
The price is £296 per night from 21 May to 22 May
£296
21 May - 22 May
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Unhinged wacko

Reviewed on 6 May 2026

Montauk Yacht Club
See all 4,777 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Havens House

You can spend an afternoon studying the exhibits at Havens House during your travels in Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.